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3-Bedroom Homes for Sale in Winter Park, FL with Private Pool

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  • /50

    $469,900 Open Mon 11:45AM - 3PM

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft

    2835 Bongart Rd, Winter Park, FL 32792

    Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

    Agent Photo

    Claudia Jenkins

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 450-7314

    2835 Bongart Rd, Winter Park, FL 32792
  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /72

    $950,000

    • 3 Beds
    • 3 Baths
    • 2,456 Sq Ft

    915 Garden Dr, Winter Park, FL 32789

    Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious Winter Park community and just a short three-minute stroll to the serene beauty of Mead Botanical Garden. A true raised ranch design, this home radiates warmth and character from the moment you arrive, featuring an expansive covered front patio that welcomes you inside.Inside, you’ll be greeted by

    Cassie Lamoureux KELLER WILLIAMS CLASSIC

    915 Garden Dr, Winter Park, FL 32789
  • /36

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,495 Sq Ft

    930 S Kentucky Ave, Winter Park, FL 32789

    Welcome home! Nestled in the heart of Winter Park this 3-bedroom, 2.5 bathroom residence offers a perfect blend of convenience, energy efficiency, and refined comfort. From the moment you enter, you'll be captivated by high ceilings and crown molding for a spacious and refined feel. The kitchen is a chef's dream featuring granite countertops, stainless steel appliances, a gas range and upgraded

    Debi Callahan ADAMS, CAMERON & CO., REALTORS

    930 S Kentucky Ave, Winter Park, FL 32789
  • /22

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    2190 Temple Dr, Winter Park, FL 32789

    BEAUTIFUL BREEZES AND EXCEPTIONAL VIEWS IN THIS STUNNING MOVE IN READY HOME LOVINGLY MAINTAINED! This immaculate home offers a perfect blend of luxury and comfort. Nestled on a tree lined street , this home welcomes you with walkways and beautifully landscaped surroundings. There’s plenty of space to enjoy everyday living & entertaining in this open & generously sized 3 bedroom, 2 baths with an

    Sharon Mikol MAINFRAME REAL ESTATE

    2190 Temple Dr, Winter Park, FL 32789
  • /43

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft

    676 Dunblane Dr, Winter Park, FL 32792

    ***PRICE IMPROVEMENT*** This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room

    Emma Kaplan BALDWIN PARK REALTY LLC

    676 Dunblane Dr, Winter Park, FL 32792
  • /68

    $960,000

    • 3 Beds
    • 2 Baths
    • 2,114 Sq Ft

    250 Cortland Ave, Winter Park, FL 32789

    Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

    Alexandra Nordine EXP REALTY LLC

    250 Cortland Ave, Winter Park, FL 32789
  • /36

    $1,050,000

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    632 Country Club Dr, Winter Park, FL 32789

    Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this

    Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    632 Country Club Dr, Winter Park, FL 32789
  • /49

    $1,097,000

    • 3 Beds
    • 3 Baths
    • 2,460 Sq Ft

    1901 Lake Sue Dr, Orlando, FL 32803

    One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. It features a modern kitchen with a marble Breakfast bar and marble countertops. An Open floor plan with lots of natural light flowing throughout. The huge primary Bedroom suite with sitting area and private bath, his and hers closets, opens to the screened pool and spa. A

    Pamela Stewart REALCOM REAL ESTATE SERVICES INC

    1901 Lake Sue Dr, Orlando, FL 32803
  • /20

    $374,900

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    2028 Leanne Ct, Winter Park, FL 32792

    Lovely pool home located in Eastbrook. This home features an open floor plan with an abundance of natural light. Recent updates include: A/C unit (2022), electrical system (2022), and a new water heater (2022). Enjoy entertaining on the patio and around the pool in the lush, landscaped backyard. The Eastbrook community is centrally located between Downtown Winter Park, UCF, shopping, and numerous

    Jamie Ampel ALL SELLERS & BUYERS REALTY INC

    2028 Leanne Ct, Winter Park, FL 32792
  • /14

    $379,999

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft

    3383 Hamlet Loop, Winter Park, FL 32792

    Charming Winter Park Home with Private Pool on Corner Lot!Don’t miss this beautifully updated 3-bedroom, 2-bath single-family home nestled in a quiet, tucked-away neighborhood in the heart of Winter Park. Just minutes from the vibrant shops and restaurants of Park Avenue, this centrally located gem offers the perfect blend of comfort, convenience, and charm.Step inside to find

    Cliff Glansen FLATFEE.COM

    3383 Hamlet Loop, Winter Park, FL 32792
  • /37

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    2758 Banchory Rd, Winter Park, FL 32792

    Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street,

    Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

    2758 Banchory Rd, Winter Park, FL 32792
  • /38

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Here is a fantastic home in Winter Park Pines, a well established and sought after community and location in Winter Park! This property is located on a corner lot and has a private pool as well as a two-car garage. This a great way to obtain home ownership at an affordable price. The construction is a Block/Brick built home making it a solid home unlike one you could buy new today. The Roof and

    Corey Cannon BHHS FLORIDA REALTY

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /74

    $1,700,000

    • 3 Beds
    • 4 Baths
    • 2,964 Sq Ft

    1270 Arlington Place, Winter Park, FL 32789

    Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

    Brian Mitnik RE/MAX 200 REALTY

    1270 Arlington Place, Winter Park, FL 32789
  • /34

    $479,900

    • 3 Beds
    • 2 Baths
    • 1,939 Sq Ft

    3054 Bluebrook Dr, Winter Park, FL 32792

    Step into your dream home located in the charming Winter Park, Florida. This stunning property boasts 3 bedrooms and 2 bathrooms, perfect for a growing family or those who love to entertain.As you enter, you are greeted by a cozy fireplace, ideal for chilly Florida evenings. The spacious living room flows seamlessly into the gourmet kitchen, complete with granite countertops and stainless steel

    Trisha Deokinandan ALORA REALTY GROUP INC

    3054 Bluebrook Dr, Winter Park, FL 32792
  • /16

    $1,449,000

    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    1644 Hibiscus Ave, Winter Park, FL 32789

    Charming, Well-Maintained Home on a Prime Lot in Winter Park’s Coveted Tree StreetsDon’t miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special

    Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

    1644 Hibiscus Ave, Winter Park, FL 32789
  • /32

    $575,000

    • 3 Beds
    • 2 Baths
    • 2,268 Sq Ft

    701 Denton Rd, Winter Park, FL 32792

    Seller will consider concessions. Seller Financing available. Contact us today. Welcome to this beautifully upgraded home in Winter Park Estates! Nestled on a quarter-acre lot, step into your private creating memories that last! This exceptional property has been meticulously maintained and enhanced with high-end features, making it a true standout. Recent upgrades include a brand-new roof

    Elizabeth Boyce CHARLES RUTENBERG REALTY ORLANDO

    701 Denton Rd, Winter Park, FL 32792
  • /30

    $459,000

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    1710 Aster Dr, Winter Park, FL 32792

    Price improvement!!! Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq feet. Nice size lot .24 acre, fenced with a large open pool featuring brand new pool equipment & newly screened patio. 2024 Updates include: NEW Roof, Luxury vinyl flooring, 5 1/4 in. baseboards, popcorn ceilings removed & retextured, Full Kitchen renovation with SS appliances, Soft close cabinets & Quartz

    Dora Siler FOLIO REALTY LLC

    1710 Aster Dr, Winter Park, FL 32792
  • /2

    $419,900

    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft

    616 Ellendale Dr, Winter Park, FL 32792

    Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home

    David Ruiz CENTRAL REALTY

    616 Ellendale Dr, Winter Park, FL 32792
  • /35

    $4,250,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 3,413 Sq Ft

    1120 Palmer Ave, Winter Park, FL 32789

    Spectacular Phil Kean Design Group whole home remodel coming soon.Miami/Coral Gables Cottage meets Winter Park Elegance.On a street of Winter Park estates this home will be a charming and sophisticated addition.Currently under construction and being reimagined for the 2026 International Builders Show "Show Home Remodel".This home will be available for occupancy in February

    Brad Grosberg PHIL KEAN REAL ESTATE LLC

    1120 Palmer Ave, Winter Park, FL 32789
  • /61

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    3308 Middlesex Rd, Orlando, FL 32803

    This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm.The magazine-worthy kitchen—featured on Southern Living’s website—boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze

    Julie Bettosini STOCKWORTH REALTY GROUP

    3308 Middlesex Rd, Orlando, FL 32803

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$607,995
Median Townhouse Sale Price
$474,000
Median 2 Bedroom Sale Price
$220,000
Median 1 Bedroom Sale Price
$155,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
312
Last 12 months Home Sales
1,023
Months of Supply
3.70
Median List Price
$525,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
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